9-[(1RS,2RS,4SR)-bicyclo[2.2.1]hept-2-yl]-6-chloro-9H-purine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-[(1RS,2RS,4SR)-bicyclo[2.2.1]hept-2-yl]-6-chloro-9H-purine
• 英文别名: NCP；9-norbornyl-6-chloropurine；9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-6-chloro-9H-purine；9-[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]-6-chloropurine
• 化学式: C₁₂H₁₃ClN₄
• 分子量: 248.715
• InChiKey: HCMOLGILLULWHJ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-[(1RS,2RS,4SR)-bicyclo[2.2.1]hept-2-yl]-6-chloro-9H-purine 在 四丁基硝酸铵 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以45%的产率得到9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-6-chloro-2-nitro-9H-purine
  参考文献：
  名称：

  SAR studies of 9-norbornylpurines as Coxsackievirus B3 inhibitors

  摘要：

  Coxsackievirus and related enteroviruses are important human pathogens that cause various diseases with clinical manifestations ranging from trivial flu-like syndromes to dangerous or even fatal diseases such as myocarditis, meningitis and encephalitis. Here, we report on our continuous SAR study focused on 9-(bicyclo[2.2.1] hept-2-yl)-9H-purines as anti-enteroviral inhibitors. The purine moiety was modified at positions 2, 6 and 8. Several analogues inhibited Coxsackievirus B3 as well as other enteroviruses at low-micromolar concentrations. The 6-chloropurine derivative was confirmed as the most active compound in this series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.070
• 作为产物：
  描述：

  (+/-)-endo-2-norborneol 、 6-氯嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到9-[(1RS,2RS,4SR)-bicyclo[2.2.1]hept-2-yl]-6-chloro-9H-purine
  参考文献：
  名称：

  新型柯萨奇病毒B3抑制剂的设计，合成和生物学评估

  摘要：

  报道了新型的柯萨奇病毒B3（CVB3）抑制剂的合成和SAR研究。这些化合物可视为在9位被各种取代的双环支架（双环[2.2.1]庚烷/烯-降冰片烷或降冰片烯）取代的6-氯嘌呤。描述了31种目标化合物的合成和生物学评估。几种类似物在低微摩尔范围（0.66–2μM）中抑制CVB3。观察到最小或没有细胞毒性。

  DOI：

  10.1016/j.bmc.2010.04.081

文献信息

• SAR studies of 9-norbornylpurines as Coxsackievirus B3 inhibitors
  作者：Michal Šála、Armando M. De Palma、Hubert Hřebabecký、Milan Dejmek、Martin Dračínský、Pieter Leyssen、Johan Neyts、Helena Mertlíková-Kaiserová、Radim Nencka

  DOI：10.1016/j.bmcl.2011.05.070

  日期：2011.7

  Coxsackievirus and related enteroviruses are important human pathogens that cause various diseases with clinical manifestations ranging from trivial flu-like syndromes to dangerous or even fatal diseases such as myocarditis, meningitis and encephalitis. Here, we report on our continuous SAR study focused on 9-(bicyclo[2.2.1] hept-2-yl)-9H-purines as anti-enteroviral inhibitors. The purine moiety was modified at positions 2, 6 and 8. Several analogues inhibited Coxsackievirus B3 as well as other enteroviruses at low-micromolar concentrations. The 6-chloropurine derivative was confirmed as the most active compound in this series. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis, and biological evaluation of novel coxsackievirus B3 inhibitors
  作者：Michal Šála、Armando M. De Palma、Hubert Hřebabecký、Radim Nencka、Martin Dračínský、Pieter Leyssen、Johan Neyts、Antonín Holý

  DOI：10.1016/j.bmc.2010.04.081

  日期：2010.6

  (CVB3) inhibitors are reported. These compounds could be considered as the 6-chloropurines substituted at position 9 with variously substituted bicyclic scaffolds (bicyclo[2.2.1]heptane/ene—norbornane or norbornene). The synthesis and biological evaluation of 31 target compounds are described. Several of the analogues inhibited CVB3 in the low micromolar range (0.66–2 μM). Minimal or no cytotoxicity was

  报道了新型的柯萨奇病毒B3（CVB3）抑制剂的合成和SAR研究。这些化合物可视为在9位被各种取代的双环支架（双环[2.2.1]庚烷/烯-降冰片烷或降冰片烯）取代的6-氯嘌呤。描述了31种目标化合物的合成和生物学评估。几种类似物在低微摩尔范围（0.66–2μM）中抑制CVB3。观察到最小或没有细胞毒性。